Social Interaction. How?

I just don't know what to do with myself lately.

I kind of feel like it's a little bit of a lack of "gatherings" that's bringing me down. I don't see very many people socially at home and I don't do it very often. My attempts at out-reaching online is stymied by the fact that most of my interactions in person are started by me being a little bit OTT and bouncy and full of open body language (mostly). The content is rarely something I put thought into. Online this does not work.

Online, I feel like I have to get past several formality barriers before I actually get to just chatting, if indeed the capability to chat uncharacteristically emerges; like a sober monologue from some alcoholic, drug-addled and hyperactive comedian that may or may not exist because he's just being used as a simile.

I suppose it doesn't help that the most recent person I started talking to online was a guy who lost his mother a week previously. I didn't know this until a few sentences in and given the various things that surrounded that, I was left with a massive hole where (I presume) normal conversation would usually lie. I asked him how his day had been and I got a "don't ask". I asked what he enjoyed doing and I got "[housework]" and "Sleeping".

The issue doesn't just run with new people though. I have at least a dozen people on Skype and MSN who I have previously spoken to at length, both online and in person. I find it almost impossible to actually start talking to them. I still leave the programs open in some hope that maybe they might see me online and be all: "Oh hey, there's Dave! I like him, we should totally talk!" (because they clearly all talk like me/the cast of Clueless). Yet still I get no conversations going.

I know that they are probably having conversations amongst themselves and not really giving this much thought. I know that I have no right to impose any sort of guilt upon them by posting this (which, sidebar, I had not actually intended to post when I started typing but I feel like I'm likely to when I'm done). I know that there are some people who I have made it awkward to talk to by my actions in the past. I know that were I to get past the starting and awkward formalities and get onto a topic of some sort, the rest would likely form itself.

Finally in the list of things-that-were-in-that-last-paragraph but is really too large an item to be in said paragraph: I know that there are a couple of people that do take the time to speak to me when I am online and I don't appreciate them as much as I should because there is often no flow in the interaction and I'm more concentrating on those people who I'm -not- managing to have an interaction with. I like that they like me but there is a key element missing from all of them that cuts it short of it feeling like a proper chat. In some cases I know what this is. In others I don't. It sucks that all things aren't equal, huh?

tl;dr

Dave knows how to write very long sentences but not how to talk to people online.